Laurel Oak Estates vs Windward at Lakewood Ranch
Two Sarasota communities, compared on the numbers that decide it — price, pace, and supply — from live MLS data as of 2026-10-24.
| Metric | Laurel Oak Estates | Windward at Lakewood Ranch |
|---|---|---|
| Median sale price | $1.33M | $612K |
| Price per sq ft | $380 | $279 |
| Avg days on market | 103 days | 50 days |
| Months of supply | 3.2 mo | 3.5 mo |
| Market | Buyer-Leaning Market | Seller's Market |
| 1-year price change | False | False |
| Recent closings | 26 | 55 |
The verdict
Laurel Oak Estates carries the higher median price — about 117% above Windward at Lakewood Ranch. Homes in Windward at Lakewood Ranch sell faster (50 days on market vs 103). Laurel Oak Estates is the tighter market on inventory (3.2 months of supply).
Where each one is
| Laurel Oak Estates | Windward at Lakewood Ranch | |
|---|---|---|
| County | Sarasota County, FL | Sarasota County, FL |
| City / area | Sarasota | Sarasota |
| ZIP | 34240, 34241 | 34230, 34240 |
Distances are straight-line; driving distance is usually 15 to 30 percent more. Flood-zone shares come from FEMA flood maps matched to sampled parcels; always check the exact address before you close.
What is for sale today
| Laurel Oak Estates | Windward at Lakewood Ranch | |
|---|---|---|
| Homes for sale now | 7 | 16 |
| Under contract | 0 | 10 |
| Asking prices today | $1.29M to $3M | $429K to $1.48M |
| Listed in the last 7 days | 0 | 9 |
| Property types listed | Single Family Residence | Single Family Residence, Villa |
Live MLS counts, refreshed with every listing pull. Browse them: Laurel Oak Estates homes for sale · Windward at Lakewood Ranch homes for sale.
The homes themselves
| Laurel Oak Estates | Windward at Lakewood Ranch | |
|---|---|---|
| Homes (parcels) | 387 | 369 |
| Built | 1990–2016 (median 1995) | 2020–2024 (median 2023) |
| Typical living area | 4,048 sq ft | 2,316 sq ft |
| Homesteaded (owner-occupied) share | 79% | 44% |
| Vacant lots | 0 | 164 |
Housing-stock figures from the Florida Department of Revenue 2025 assessment roll (public records).
Price history, year by year
| Year | Laurel Oak Estates median | Windward at Lakewood Ranch median |
|---|---|---|
| 2022 | $1.3M (11 sales) | $420K (9 sales) |
| 2023 | $1.26M (6 sales) | $783K (16 sales) |
| 2024 | $1.48M (21 sales) | $1.1M (41 sales) |
| 2025 | $1.48M (27 sales) | $684K (26 sales) |
| 2026 | $1.32M (22 sales) | $616K (26 sales) |
Since 2022, Laurel Oak Estates's median sale price is +2% and Windward at Lakewood Ranch's is +47% — Windward at Lakewood Ranch has appreciated faster over that stretch.
How each one trades
| Laurel Oak Estates | Windward at Lakewood Ranch | |
|---|---|---|
| Sale-to-original-list | 92.5% | 100.0% |
| New-construction share of sales | 0% | 85% |
| Typical sold home | 3,393 sq ft | 2,088 sq ft |
Last 12 months of recorded closings; sale-to-original-list is the share of the first asking price sellers actually got.
Schools the listings are zoned for
| Laurel Oak Estates | Windward at Lakewood Ranch | |
|---|---|---|
| Elementary | Tatum Ridge Elementary | Tatum Ridge Elementary |
| Middle | Mcintosh Middle | Mcintosh Middle |
| High school | Sarasota High | Booker High |
The school most often recorded on each community's MLS listings. Always confirm a specific address with the district.
Which one fits
On budget alone, Windward at Lakewood Ranch is the lower entry point (median $612K vs $1.33M). Buyers who want newer construction (fewer near-term roof, HVAC and re-plumb items, and easier insurance quotes in Florida) will find it in Windward at Lakewood Ranch; Laurel Oak Estates trades that for a more established street and, typically, larger lots. Sellers get a faster sale in Windward at Lakewood Ranch (50 days on market on average); buyers get more negotiating room where homes sit longer.
Neither number set decides it: drive both on a weekday evening, check the HOA documents and the flood zone for the exact street, and price the insurance before you write an offer. A Momentum agent who works both communities can pull the comparable sales for any two specific homes.
Questions people ask
Is Laurel Oak Estates more expensive than Windward at Lakewood Ranch?
Yes, on recent sales: the median sale price in Laurel Oak Estates is $1,330,000 versus $612,000 in Windward at Lakewood Ranch, about 117% higher.
Which has newer homes, Laurel Oak Estates or Windward at Lakewood Ranch?
Windward at Lakewood Ranch: its homes were built 2020–2024 with a median year of 2023, versus a median of 1995 in Laurel Oak Estates (Florida DOR assessment roll).
Which has bigger homes?
Laurel Oak Estates. The typical home there is 4,048 sq ft of living area, versus 2,316 sq ft in Windward at Lakewood Ranch.
Which has appreciated more, Laurel Oak Estates or Windward at Lakewood Ranch?
From 2022 to 2026 the median sale price rose 2% in Laurel Oak Estates and 47% in Windward at Lakewood Ranch (recorded MLS closings by calendar year).
Where do sellers get closer to asking price?
Windward at Lakewood Ranch — sellers there received 100.0% of the original list price over the last 12 months versus 92.5% in Laurel Oak Estates.
What high schools serve Laurel Oak Estates and Windward at Lakewood Ranch?
Listings in Laurel Oak Estates most often report Sarasota High; listings in Windward at Lakewood Ranch report Booker High. Zoning is set by the district and can change - verify by address.
Go deeper on each: Laurel Oak Estates homes, photos & schools · Windward at Lakewood Ranch homes, photos & schools
Figures are aggregates from realMLS / DBAAR, updated regularly. Thinking about either? Talk to Momentum Realty.